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Vacation rentals in Midway

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Top-rated vacation rentals in Midway

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home in Midway
Bit and Bourbon
Located in the heart of historic downtown Midway, this private, tucked away home has been fully renovated. It features two bedrooms with king sized beds, two bathrooms, a full sized kitchen, quaint dining room, and living room. This home is just a walk around the corner from shops and restaurants. Within minutes from Keeneland, the Kentucky Horse Park, Frankfort, and Lexington. This makes it ideal to tour the bourbon trail as well. A bonus is an electric charging station in the parking lot!
$257 per night
Rental unit in Midway
Downtown Midway Loft--Walk Everywhere!
Located in the heart of downtown Midway, this renovated studio apartment in an 1890's Whiskey Warehouse makes for the perfect retreat. The bedroom features a queen sized Tempur-Pedic mattress, ROKU TV, and desk. Plan your day with a morning coffee in the full kitchen that's equipped with basic cookware for prepping light meals. The apartment is located on the third floor, so pack light as it is accessed only by stairs. We delight to host your stay in beautiful Kentucky!
$124 per night
Farm stay in Midway
Wintergreen Cottage
Located in the heart of horse country, the Wintergreen cottage is situated on a working Thoroughbred farm with a fascinating history and a prime location. Wintergreen is just minutes from downtown Midway, with a variety of local shops & renowned restaurants. Wintergreen is less than 20 minutes from Keeneland and multiple distilleries on the Kentucky Bourbon Trail, and is near the Kentucky Horse Park, Old Friends, as well as a multitude of wineries and breweries.
$148 per night

Stay near Midway's top sights

Photo of The Brown Barrel & Blind Harry's
The Brown Barrel & Blind Harry's12 locals recommend
Photo of The Goose & Gander
The Goose & Gander11 locals recommend
Photo of Mezzo Italian Cafe and Provisions
Mezzo Italian Cafe and Provisions8 locals recommend
Photo of Holly Hill Inn
Holly Hill Inn26 locals recommend
Photo of Heirloom Restaurant
Heirloom Restaurant30 locals recommend
Photo of Darlin Jean's Apple Cobbler Cafe
Darlin Jean's Apple Cobbler Cafe9 locals recommend

Other great vacation rentals in Midway

Rental unit in Midway
Modern Remodeled Downtown Midway Studio
$140 per night
Private room in Midway
Make your stay in Midway special
$76 per night
Rental unit in Midway
Trackside Suite
$170 per night
Cabin in Midway
Kentucky breeze cabin
$233 per night
Home in Midway
Perfect Access to All Things Bluegrass & Horses
$189 per night
Farm stay in Versailles
Bluegrass Country Cottage
$157 per night
Home in Midway
Country Cottage in Horse and Bourbon Country
$140 per night
Rental unit in Versailles
High style on the Bourbon Trail
$116 per night
Home in Stamping Ground
Buffalo Springs Distilling Company
$154 per night
Home in Lexington
Silver Streak Equestrian Horse Haven
$79 per night
Cabin in Lawrenceburg
River Front Cabin - Hot tub - Bourbon Trail
$258 per night
Townhouse in Frankfort
Bourbon Trail Lakehouse in Horse Country!
$150 per night
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  5. Midway